CN103709139A - 无水右兰索拉唑的制备方法 - Google Patents
无水右兰索拉唑的制备方法 Download PDFInfo
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- CN103709139A CN103709139A CN201210380902.3A CN201210380902A CN103709139A CN 103709139 A CN103709139 A CN 103709139A CN 201210380902 A CN201210380902 A CN 201210380902A CN 103709139 A CN103709139 A CN 103709139A
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- CN
- China
- Prior art keywords
- lansoprazole
- methods
- anhydrous
- drying
- hydrate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- MJIHNNLFOKEZEW-RUZDIDTESA-N dexlansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1C[S@@](=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-RUZDIDTESA-N 0.000 title claims abstract description 100
- 238000002360 preparation method Methods 0.000 title abstract description 25
- 229940008871 dexilant Drugs 0.000 title abstract 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000010992 reflux Methods 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012046 mixed solvent Substances 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 229960003568 dexlansoprazole Drugs 0.000 claims description 92
- 238000000034 method Methods 0.000 claims description 45
- 239000007787 solid Substances 0.000 claims description 32
- 238000003756 stirring Methods 0.000 claims description 24
- 238000001291 vacuum drying Methods 0.000 claims description 18
- 238000001035 drying Methods 0.000 claims description 16
- 238000001816 cooling Methods 0.000 claims description 11
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 11
- 238000005406 washing Methods 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000013078 crystal Substances 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 6
- 239000012452 mother liquor Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 2
- 238000000926 separation method Methods 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000011343 solid material Substances 0.000 abstract 4
- 238000002844 melting Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- JILHZKWLEAKYRC-UHFFFAOYSA-N 1-methoxy-2,2-dimethylpropane Chemical compound COCC(C)(C)C JILHZKWLEAKYRC-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 14
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- 239000012065 filter cake Substances 0.000 description 10
- -1 yield 90% Substances 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000013270 controlled release Methods 0.000 description 3
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229960003174 lansoprazole Drugs 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 206010063655 Erosive oesophagitis Diseases 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- CAQXGPRORCTUAZ-UHFFFAOYSA-N acetonitrile;n,n-diethylethanamine;hydrate Chemical compound O.CC#N.CCN(CC)CC CAQXGPRORCTUAZ-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 208000024798 heartburn Diseases 0.000 description 1
- MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 229940126409 proton pump inhibitor Drugs 0.000 description 1
- 239000000612 proton pump inhibitor Substances 0.000 description 1
- 238000013094 purity test Methods 0.000 description 1
- 208000024981 pyrosis Diseases 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Claims (25)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201210380902.3A CN103709139B (zh) | 2012-10-09 | 2012-10-09 | 无水右兰索拉唑的制备方法 |
Applications Claiming Priority (1)
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CN201210380902.3A CN103709139B (zh) | 2012-10-09 | 2012-10-09 | 无水右兰索拉唑的制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN103709139A true CN103709139A (zh) | 2014-04-09 |
CN103709139B CN103709139B (zh) | 2016-12-21 |
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CN201210380902.3A Active CN103709139B (zh) | 2012-10-09 | 2012-10-09 | 无水右兰索拉唑的制备方法 |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104177333A (zh) * | 2013-05-24 | 2014-12-03 | 四川海思科制药有限公司 | 一种理化性质稳定的(r)-2-[[[3-甲基-4-(2,2,2-三氟乙氧基)-2-吡啶基]甲基]亚磺酰基]-1h-苯并咪唑 |
CN104483403A (zh) * | 2014-12-05 | 2015-04-01 | 广东东阳光药业有限公司 | 一种检测右兰索拉唑原料药有关物质的方法 |
CN106279107A (zh) * | 2016-08-10 | 2017-01-04 | 成都尚药科技有限公司 | 一种右旋兰索拉唑晶型的制备方法 |
CN107459506A (zh) * | 2017-09-30 | 2017-12-12 | 南京优科生物医药研究有限公司 | 一种无水右旋兰索拉唑的制备方法 |
CN108586307A (zh) * | 2018-05-31 | 2018-09-28 | 成都市科隆化学品有限公司 | 一种无水芴甲氧羰基-l-脯氨酸的制备方法 |
CN109265497A (zh) * | 2018-10-18 | 2019-01-25 | 武汉中科光谷绿色生物技术有限公司 | 一种利用有机溶剂转化n-乙酰神经氨酸水合物制备n-乙酰神经氨酸的方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1355798A (zh) * | 1999-06-17 | 2002-06-26 | 武田药品工业株式会社 | 苯并咪唑化合物结晶 |
-
2012
- 2012-10-09 CN CN201210380902.3A patent/CN103709139B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1355798A (zh) * | 1999-06-17 | 2002-06-26 | 武田药品工业株式会社 | 苯并咪唑化合物结晶 |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104177333A (zh) * | 2013-05-24 | 2014-12-03 | 四川海思科制药有限公司 | 一种理化性质稳定的(r)-2-[[[3-甲基-4-(2,2,2-三氟乙氧基)-2-吡啶基]甲基]亚磺酰基]-1h-苯并咪唑 |
CN104483403A (zh) * | 2014-12-05 | 2015-04-01 | 广东东阳光药业有限公司 | 一种检测右兰索拉唑原料药有关物质的方法 |
CN104483403B (zh) * | 2014-12-05 | 2016-06-01 | 广东东阳光药业有限公司 | 一种检测右兰索拉唑原料药有关物质的方法 |
CN106279107A (zh) * | 2016-08-10 | 2017-01-04 | 成都尚药科技有限公司 | 一种右旋兰索拉唑晶型的制备方法 |
CN107459506A (zh) * | 2017-09-30 | 2017-12-12 | 南京优科生物医药研究有限公司 | 一种无水右旋兰索拉唑的制备方法 |
CN108586307A (zh) * | 2018-05-31 | 2018-09-28 | 成都市科隆化学品有限公司 | 一种无水芴甲氧羰基-l-脯氨酸的制备方法 |
CN109265497A (zh) * | 2018-10-18 | 2019-01-25 | 武汉中科光谷绿色生物技术有限公司 | 一种利用有机溶剂转化n-乙酰神经氨酸水合物制备n-乙酰神经氨酸的方法 |
CN109265497B (zh) * | 2018-10-18 | 2022-04-19 | 武汉中科光谷绿色生物技术有限公司 | 一种利用有机溶剂转化n-乙酰神经氨酸水合物制备n-乙酰神经氨酸的方法 |
Also Published As
Publication number | Publication date |
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CN103709139B (zh) | 2016-12-21 |
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Legal Events
Date | Code | Title | Description |
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C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right |
Effective date of registration: 20190515 Address after: Room 304-12, 665 Zhangjiang Road, Shanghai Free Trade Pilot Area, 201210 Patentee after: Shanghai Huilun Pharmaceutical Technology Co.,Ltd. Address before: Room 650-10, Building No. 2, 351 Guoshoujing Road, Zhangjiang High-tech Park, Pudong New Area, Shanghai, 201203 Patentee before: SHANGHAI HUILUN LIFE SCIENCE & TECHNOLOGY Co.,Ltd. |
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TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20190819 Address after: Room 650-10, Building No. 2, 351 Guoshoujing Road, Shanghai Free Trade Pilot Area, 201203 Patentee after: SHANGHAI HUILUN LIFE SCIENCE & TECHNOLOGY Co.,Ltd. Address before: Room 304-12, 665 Zhangjiang Road, Shanghai Free Trade Pilot Area, 201210 Patentee before: Shanghai Huilun Pharmaceutical Technology Co.,Ltd. |
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CP01 | Change in the name or title of a patent holder | ||
CP01 | Change in the name or title of a patent holder |
Address after: Room 650-10, Building No. 2, 351 Guoshoujing Road, Shanghai Free Trade Pilot Area, 201203 Patentee after: Shanghai Hui Bio Technology Co.,Ltd. Address before: Room 650-10, Building No. 2, 351 Guoshoujing Road, Shanghai Free Trade Pilot Area, 201203 Patentee before: SHANGHAI HUILUN LIFE SCIENCE & TECHNOLOGY Co.,Ltd. |
|
CP03 | Change of name, title or address | ||
CP03 | Change of name, title or address |
Address after: 200241 floor 10, building 5, No. 525, Yuanjiang Road, Minhang District, Shanghai Patentee after: Shanghai Huilun Pharmaceutical Co.,Ltd. Address before: Room 650-10, building 2, 351 GuoShouJing Road, Shanghai pilot Free Trade Zone, 201203 Patentee before: Shanghai Hui Bio Technology Co.,Ltd. |